Facile conversion of 4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one into carbocyclic 2′-deoxyribonucleoside analogues

Abstract

The readily available 3,5-syn-disubstituted cyclopentenes 9–13 react with N-bromosuccinimide (or N-bromoacetamide) and silver acetate in glacial acetic acid in a highly stereoselective manner to furnish the bromoacetates 14–18 in good yields. A plausible explanation for the observed selectivity is proposed. Hydrodebromination of compounds 14, 17, 18 and 19 provided the corresponding 2′-deoxyribonucleoside analogues 20–23.